Thank you to Rocker for pointing out Naruto's AP advantage. I wasn't sure if the high or low version of the calc was accepted. But I'd assume the high was accepted, otherwise it would be an AP stomp.
To get to my reasoning.
Tsuna not having access to the two greatest attacks in his arsenal severely cripples him here, as they are both ranged attacks, which is his greatest advantage in this fight, paired with his flight.
This is sage mode Naruto from the Pain arc. Naruto in general is rather unlikely to use genjutsu, but, obviously, he spams shadow clones, toad summons and rasengan like no one's business. Only thing he can't spam, but still do a few times, is the rasenshuriken.
Naruto has the clear ground advantage. Duplication, toad summons, and all manner of rasengan given him numerous tools on the ground. Toad song and kwaze kumite (I think that's what it's called) given him even more of a versatility advantage, for not only can he paralyze, but his physical attacks don't even have to connect for Tsuna to be hit. Though, arguably, Tsuna's hyper intuition would likely tell him something is up with Naruto's attack. His hyper intuition is nothing more than a somewhat inconsistent danger sense, which also allows him to figure things out much more quickly than the average hitman. It also allows him to have some degree of resistance to illusions, and tell him when he has been caught in one, like when he fought against Torikabuto. Tsuna used an X-Burner to physically bust his way out of the illusion. The X-Burner is banned here, but it should be noted that it's possible for Tsuna to manage to physically bust through illusions. But it's highly unlikely given that the X-Burner is banned here.
However, I do believe Tsuna would win for the following reasons. First and foremost, is his flight, which Tsuna abuses, and rightfully so. If the opponent is stronger than him, such as in the fight against Genkishi, he will simply fly away, and come up with a strategy. For Naruto to even reach Tsuna, will require energy on his behalf, while Tsuna can, rather casually, weave in and out of Naruto's attacks. Of course, it would be problematic is Naruto tossed a rasenshuriken at Tsuna. However, as it's a chakra attack, Tsuna could absorb the entirety of it, bridging some of the AP gap, and becoming even faster, making his strategy of flight and fight far more effective.
However, his second key to winning, is his Zero Point Breakthrough: First Edition. Naruto's summons and clones are nothing but bunches of Chakra, which Tsuna can freeze by merely touching them. Seeing as how the clones would be trying to attack him anyway, First Edition gives him a rather simply way to dispatch of them, and the toads as well. If the toads imbue their weapons with Chakra, he could freeze those as well. The toads would have to use some kind of fire style to melt the ice, but I can't recall how in character it would be for them to do such, and that's also assuming their entire body isn't frozen. Freezing an entire body isn't instant, but it's quick enough for people like Byakuran, or Tozaru to not react to their attacks or box weapons being frozen. Though you can ignore the Byakuran example, as this is choice arc Tsuna.
Not to mention that Tsuna has augmented defense with his cloak, and pertification with Natsu. So here, not only does First Edition serve as a way to deal with clones, and toad summons, but so does petrification. Not to mention that First Edition can freeze attacks as well. Though Tsuna is less likely to try this, as it's more dangerous for him. In particular given Naruto's AP advantage.
Tsuna merely has ways to out all of his options, not to mention that his casual flight forces Naruto to expend energy to mere approach Tsuna, while Tsuna's energy expense is rather negligible when it comes to flight. Naruto's versatility in his summons and clones are taken care of by First Edition or Petrification, and a couple of his tricks will simply be avoided due to Tsuna's intuition, or at least have their effectiveness decreased. Landing a frog song on such a mobile target such as Tsuna is rather unlikely, but Natsu can roar and keep most things at bay with the sky flame's harmony attribute. As Naruto would be petrified in he got too close.
All in all, Tsuna has all the tools necessary to win this one. So I'd go with him, Mid-High diff.
